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Jon Stewart’s new Apple TV+ series: Old man yells at cloud—but it hits the spot

Enlarge / Jon Stewart is back on TV to set some things on fire.
Apple TV+ / Busboy

In Jon Stewart’s first-ever conversation with an Apple TV+ studio audience, he offers a curious send-off—in fact, it argues against the point of his new multi-million dollar hosting deal. “You’re probably just going to look at aggregated clips of” this first episode of The Problem With Jon Stewart, he says, instead of subscribing to Apple TV+. It’s a bit meandering, followed by a joke about pirating episodes of Ted Lasso.

If anybody can show up to a new streaming service and make a joke at the expense of subscriptions, it’s probably Stewart. Online video sharing—and we’re talking the renegade kind, uploaded by fans and shared freely—greatly contributed to The Daily Show‘s massive cultural footprint before Stewart left that show behind in 2015. And as you may have noticed, the TV landscape has dramatically changed since then. These days, every major player is throwing stuff at the video-streaming wall to see what sticks (or, in Quibi’s case last year, what absolutely doesn’t).

So after six years off the “fake news” desk, what path does Stewart and Apple’s new production take? His aforementioned joke may suggest a series that’s meant to be shared and remixed in small clips, but The Problem arrives with a different modus operandi: empathy, not sound bites, and patience, not pulverization. You can arguably pluck out some zingers tailor-made for quick swipes on a service like TikTok, but Stewart seems more invested in relishing the full 44 minutes of each episode. As a result, this fake-news innovator spends the runtime of his new series punting the “fake” out of his reputation, expectations be damned.

Gentle corralling of charged conversations

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Enlarge / Jon Stewart jokes in the first episode about “looking like this now.”
Apple TV+ / Busboy

At some point today, if not already, the series’ pilot episode will go live, and it revolves around US veterans. In particular, it homes-in squarely on the aggravating issue of “burn pits,” and how the US’s decision to dispose of wartime waste via acres-wide burning sites (reportedly a mix of human flesh, toxic waste, and other trash) appears to have caused cancer in vets who’d toured through Afghanistan and Iraq. The series’s second episode, which lands in two weeks but I’ve also seen, focuses on the general topic of “freedom” and veers in a few directions, ranging from American anti-vaxxers to how free speech is threatened around the world.

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Neither begins with a topical, headline-filled monologue, and neither includes chats with stand-up comedians faking as “senior correspondents.” Though both episodes open with a smattering of jokes, often at Stewart’s own expense, it doesn’t take long for him to settle into his apparent dream role: a Dan Rather-caliber newscaster who runs a news program at the local dive bar. F-bombs and pointed drops of “are you #$#$ing kidding me” punctuate his reporting-filled breakdowns of whatever topic’s at hand, and he’s happy to let anger boil over when talking about aggrieved veterans—a topic he’s been front-and-center about in the public eye since testifying on Capitol Hill about the 9/11 First Responders’ bill.

Both episodes include a similar formula: Stewart opens alone at his desk to break down a story, comment on news clips, and alternate between jokes and rants. Then pre-filmed skits emerge during one or two fake commercial breaks. And finally, Stewart hosts a roundtable panel with at least three interviewees, where he’s careful to split the difference between letting guests open up about their expertise and interrupting to move the conversation along. The latter is easily the best part in this early series gestation period, and it plays out almost exactly like you might expect from someone who previously made criticism of Crossfire and Fox News an extracurricular hobby. Any American who has ever tuned-in to overseas cable news panel discussions and thought, “Oh, this isn’t awful” will appreciate Stewart’s gentle corralling of these charged conversations.

The cough heard ’round the studio (twice)

But it’s clear why Apple TV+ provided two episodes to the press ahead of the pilot’s Thursday premiere—the first episode is rough. Stewart steers his “comedian at a desk” ship into new waters, and the studio audience isn’t necessarily along for the ride. They’re mostly silent as they realize that this show, which looks a lot like the current Daily Show, or Last Week With John Oliver, or Full Frontal with Samantha Bee, or even The Late Show with Stephen Colbert, foregoes those series’ typical mathematical formula, which is essentially one joke for every 3-4 “serious” allegations or news reminders. Stewart seems content to let the subject matter guide his emotions into honest, frank, and angry places instead of hiding his emotions behind punchlines.

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Even though the second episode finds its footing—finally, viewers feel like they’re at the bar with Jon and at his level, instead of him talking to viewers from on high—its inclusion of a studio audience during a lengthy serious-news panel discussion lands weirdly. We hear someone in the quiet crowd cough during one question, and they return to their cough about a minute later, almost as if they’re trying to get someone’s attention (like, “honey, maybe we should, ya know, leave and check the parking meter”). I noticed this, admittedly, while I’d switched from the couch to my kitchen, headphones on, washing dishes and taking in the conversation as if it were a podcast.

Coincidentally, each episode comes with a companion podcast episode, and these are where you’ll hear from Stewart’s writers and producers, since those voices are otherwise mostly muted in the Apple TV+ series itself. During each Apple TV+ episode, we get a few peeks behind the scenes at The Problem‘s production halls, peppered by his staff’s jokes and replies. But Stewart is absolutely running the show in these moments, too. The most dramatic example comes when his staff asks him what he fears about his upcoming interview with Denis McDonough, US Secretary of Veterans Affairs, about burn pits. Stewart rattles off a few sound bites, pretending to be McDonough, then turns back to his normal voice: “They’ll just give bullshit.”

Minutes later, we watch McDonough offer some of those very expected sound bites, which Stewart is at least quick to jump on and create an interesting conversation out of. This comes moments after Stewart admits, while micing up, that “in all my years at The Daily Show, I never did this—actually went and interviewed somebody.” At least in the case of the McDonough interview, we’re light years beyond Daily Show territory. Stewart isn’t interested in either mocking his interview subject or himself, and his show’s long runtime lets him keep the conversation mostly intact. You’ll watch McDonough try, but fail, to run circles around Stewart. The secretary offers tons of empathetic rhetoric for US vets, but Stewart’s format opts not to lop any of those lines off as nice-sounding pledges to veterans. We instead hear those lines repeated without satisfying answers to Stewart’s clear and fair questions.

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The result isn’t funny, but it sure is fantastic.

What’s! More! Hitler!

The Problem With Jon Stewart. This one pops up at the end of the second episode as an Apple TV+ fakeout, looking like a series suggestion while also adding to the episode’s jokes about anti-maskers.”>
Enlarge / An example of visual gags in The Problem With Jon Stewart. This one pops up at the end of the second episode as an Apple TV+ fakeout, looking like a series suggestion while also adding to the episode’s jokes about anti-maskers.
Apple / Busboy

Stewart can’t help but take himself down a peg whenever possible, particularly when he jokes that this series will make it harder for him to hang out with comedians at clubs like the Comedy Cellar without getting mocked for being so serious. He also shows a willingness to go into sillier territory when episodes don’t hinge so largely on heartwrenching stories of US veterans. The “freedom” episode includes a full segment which opens with the full studio audience shouting its name, as if it were a game show: “What’s! More! Hitler!” A later “commercial break” sees famed documentarian Ken Burns host a brief segment titled “Ken’s burns,” in which he makes elaborate, obtuse jokes at other people’s expense.

Ultimately, Stewart opens his new series more interested in the things that light a fire under his own butt, perhaps to make a point that “funny news” in the year 2021 needs more “news,” less “funny.” The most memeable and shareable stuff comes not from jokes but from the charged statements made by panelists. In a charged speech, one veteran suggests that the US would “go to war” against a nation that left its vets so unsupported. A persecuted journalist in the Philippines points to research that suggests social media users who follow far-right or far-left leaders themselves become that much more entrenched in far-right or far-left politics in less than two years. And she says that to urge the worldwide community to mind how companies like Facebook are gamed by dictators in order to lead their constituents by the nose with falsehoods.

It seems like Stewart doesn’t care how we hear those messages, so long as we do. Should you have the patience for 44 minutes of nuanced, uncensored dives into deeply reported subject matter—and can stomach segments without as many punchlines as you’re used to from this format—I suggest you clear your schedule and put down your smartphone to absorb old Jon Stewart’s new Apple TV+ tricks.

The Problem with Jon Stewart debuts tonight on Apple TV+ with new episodes arriving on every two weeks on Thursdays.

The Problem with Jon Stewart trailer